Stereoselective N-Glycosylation by Staudinger Ligation
- 30 October 2004
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 6 (24) , 4479-4482
- https://doi.org/10.1021/ol048271s
Abstract
Stereoselective methods for the chemical synthesis of β-N-glycosyl amides are needed to generate glycopeptides and glycoproteins. Here, we report that the Staudinger ligation can be used to form glycosylated asparagine derivatives. The reaction proceeds with high stereoselectivity, and a variety of glycosyl azides can function as substrates. Our results provide precedence for the use of this powerful amide-bond-forming reaction for N-glycopeptide synthesis.Keywords
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